Destroyer OC Question

[ayel91]

#58, Destroyer OC 2012.

Carbonyl deactivating, Amide activating o/p. Got that.
1. Reacting with primary, secondary, etc amines with a Lewis Acid causes the Nitrogen to attack Fe? Thereby causing it to be meta directing?
2. If that's not right, doesn't Chlorination of aniline occur at all ortho and para sites?
1st isn't an answer choice and answer says E) the meta chlorination is incorrect.

Answer says monochlorinated at para is major and monochlorinated at ortho is minor. Doesn't probability count? There being 2 ortho positions as opposed to 1 para, why is para the major product?

 

[Xo1991]

View attachment 24288

#58, Destroyer OC 2012.

Carbonyl deactivating, Amide activating o/p. Got that.
1. Reacting with primary, secondary, etc amines with a Lewis Acid causes the Nitrogen to attack Fe? Thereby causing it to be meta directing?
2. If that's not right, doesn't Chlorination of aniline occur at all ortho and para sites?
1st isn't an answer choice and answer says E) the meta chlorination is incorrect.

Answer says monochlorinated at para is major and monochlorinated at ortho is minor. Doesn't probability count? There being 2 ortho positions as opposed to 1 para, why is para the major product?

Para is the major product because it is less sterically hindered

 

[patricklin27]

you can go both ways with this. one could say that the chlorine on the ortho position is the major product because it draws electrons away from the withdrawing group (NH2) thus making it more stable.